title: InBr3-catalyzed glycosidation of glycals with arylamines: an alternative approach to access 4-aminocyclopent-2-enones.
abstract: To turn side products into major products, a novel strategy to access biologically active 4-aminocyclopent-2-enones was developed. These compounds were originally identified as side products but became major products when 3,5-dimethylpyran-3,4-diol 7a was used as the substrate and 30% InBr(3) as the catalyst. Aryl- or heteroarylamines as well as variously substituted glycals can be used in this reaction, and the corresponding 4-aminocyclopent-2-enones were obtained in moderate to good yields. These compounds can be further used to prepare 4-aminocarbocyclic nucleosides.
authors.affiliation: Department of Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, China.
authors.forename: Fulong
authors.initials: F
authors.lastname: Li
authors.forename: Chunyong
authors.initials: C
authors.lastname: Ding
authors.forename: Meining
authors.initials: M
authors.lastname: Wang
authors.forename: Qizheng
authors.initials: Q
authors.lastname: Yao
authors.forename: Ao
authors.initials: A
authors.lastname: Zhang
mesh_terms: D000588:Amines / Q000737:chemistry; D000998:Antiviral Agents / Q000138:chemical synthesis*; D002384:Catalysis; D003517:Cyclopentanes / Q000138:chemical synthesis*; D006027:Glycosides / Q000737:chemistry; D007204:Indium / Q000737:chemistry*; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis; D011453:Prostaglandins / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000588:Amines; D000998:Antiviral Agents; D003517:Cyclopentanes; D006027:Glycosides; D009705:Nucleosides; D011453:Prostaglandins; C530781:indium bromide; D007204:Indium; C007201:cyclopentanone